Epimerization of CarbohydratesviaStannylene Acetals. A Practical Synthesis of D-Talose1
作者:
György Hodosi,
Pavol Kováč,
期刊:
Journal of Carbohydrate Chemistry
(Taylor Available online 1998)
卷期:
Volume 17,
issue 4-5
页码: 557-565
ISSN:0732-8303
年代: 1998
DOI:10.1080/07328309808002337
出版商: Taylor & Francis Group
数据来源: Taylor
摘要:
When treated with Bu2SnO in a suitable solvent, reducing sugars preferentially form 1,2-O-stannylene acetals and, on prolonged treatment with a slight excess of the reagent at reflux temperature, they undergo epimerization. This allows simple preparation of rare monosaccharides from readily available, unprotected starting materials. The process is equilibrium driven, and the equilibrium is shifted largely in favor of structures having an axial hydroxyl group at position 2.
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